"Ten Men: Jon Stewart"
July 2001
by A.J. Jacobs
Annotated by Jon Stewart


(Editor's note: Photos of this article are available here. Everything in Jon's handwriting is in [brackets]. Everything in bold is stuff Jon highlighted or circled. Some graphics could not be reproduced in text, e.g., Jon playing tic-tac-toe in the margins. See the pics for those details.)

The smartest, most innovative show on TV is not Frontline or Nightline . . . or any Line. It is a small news show on Comedy Central hosted by a wiseass kid from New Jersey who has to comment on everything. [Annotated by Jon Stewart]

Jon Stewart didn't want us to write this profile. [This is bullshit. What a hatchet job. Who do you people think you ... oh wait ... there's more.] Well, he wasn't sure anyway. I pleaded, his publicist begged, but Stewart had to think about it, let us sweat a little. So was he being a bit of a diva, I ask later? No, he insists. Just insecure. Stewart says he was worried an Esquire cover was simply too much of a good thing. He's on a roll like no other in his thirty-seven years, [I'm 38, although I'm told I can play 37.] and he thought maybe, just maybe, this would kick off a backlash.

"It's like the Skittles commercial," he explains. "The Skittles rainbow comes up and all the Skittles come ring down and you start to wonder, When are they going to run out of Skittles?" He's got a point, I suppose. Aside from the occasional misstep -- the lukewarm Grammy Awards gig comes to mind -- [Here's something sad. I thought that went well.] life has been pretty sweet of late for this shortish Jewish guy from Jersey. Consider: He was just profiled by 60 Minutes. ("At first I thought they were coming because of that organ donor business I run out of my backyard," he says.") [Excellent use of a parenthetical.] He recently got married. He and his colleagues snagged a Peabody Award. ("I was excited when I found out what it was.") [Way too much. The parenthetical thing's gettin' old.] And he gets paid $1.5 million [Lira] a year to do a fake news program -- The Daily Show with Jon Stewart, on Comedy Central -- that just happens to provide the smartest comedy on TV.

Stewart tells me about his Skittles-and-skittishness theory one night after the show. We're in his Manhattan office -- exposed brick, gum-ball machines, Neil Diamond poster [It's actually Lenny Bruce. But you know how we all look alike.] -- and I've finally got him for a couple hours. My notebook's out, my recorder's on, and I'm ready to hear about his rise from high school outcast to kiddie-show puppeteer to host of the town. [I bet it's a fascinating sto ... zzzzzzzzz]

Only problem is, Stewart refuses to stay on topic. He has his TV on CNN, and the man can't stop watching it over my shoulder. A newscaster us talking about Aaron Sorkin, the creator of the West Wing, who has been busted for psychedelic mushrooms. "Can you believe that to create a show about government that seems relevant, the guy had to be on mushrooms? That's fucking pathetic."

Stewart takes a swig [Can you swig bottled water?] of his Poland Spring, wipes his mouth. He's somewhere between bemused and mildly pissed. Okay, um, we were discussing your childhood in Jersey . . . .

"Oh, come on," he says. CNN is now covering the scandal over Jackass, the MTV show accused of inspiring deadly copycat stunts. "Don't they know that teenagers are going to do retarded things without Jackass? What about cartoons? When you were a kid, didn't you ever put up an enormous rubber band and then slingshot yourself on roller skates after a quickly moving bird?" [<-- True Story.]

Stewart grabs a Wilson football from his desk and starts tossing it in the air. Despite vigorous scrubbing, he's still got that hint of that weird beige anchorman make up on his face. [My actual skin color.] He's five foot six [I'm 5'7", but I'm told I can play 5'6".] and his head is slightly oversized and he's started to gray around the temples, but he's relatively handsome man. Cute, the girls call him. He's wearing a blue sweatshirt with the sleeves pulled up to expose arm hair [Enough. People may be eating.] which is abundant enough to insulate him though those cold New York winters. [Sexist!!! Would you be so concerned about my appearance if I were a woman? A woman with a penis?]

So you were saying about Jersey . . . The phone rings. It's Stewart's wife, Trac[e]y, a veterinary student. Earlier today, Trac[ie] came to the office and tidied up-newspapers, unopened packages, the occasional Playboy, everything in stacks and boxes. Like any man, Stewart's got mixed feelings about this. "You found a piece of babka on my desk?" He says to Trac[ee]. "From Chanukah? Oh, my God! Was it good?" ["Jewey Jew a piece of Jew on my Jew?" he says to Tracey. "From Jewekah? Oh my Jew. Was it Jewey?"] Since Stewart's distracted, we'll have to get back to childhood stuff. [Oh good] In the meantime, take note: His Daily Show is to current comedy what Saturday Night Live was to '70s comedy -- surprising, groundbreaking, and sure to be imitated. Haven't seen it? Go up your dial, way up, a couple clicks past the Spanish guy in the bee costume (Stewart's joke). [Heelarius]. There, every weekday dressed in a suit and tie, Stewart sits behind a desk in midtown New York, shuffles some papers, looks at the camera, and completely and totally subverts the media establishment. Think of Leno's monologue, but far more cerebral. Think H.L. Mencken, but with hair gel. [Think Conrad Bain but with a superfluous nipple. Think Napoleon but with attitude ... for the '90s ... on acid.]

Stewart kicks of the show with a series of faux headlines, [This may all be correct. I've never actually seen the program.] the best of which take aim at the bloated Hollywood-Washington machine, such as this one, about the Golden Globes: "Julia Roberts came accompanied by the sun -- which shines only for her." Throughout the half hour, Stewart will throw one of his five "correspondents" -- Mo Rocca, Steve Carell, Vance DeGeneres, Stephen Colbert, and Nancy Walls -- who mock field reports as deftly as he mocks anchors. Watch Carell do an inflammatory investigation on the latest threat to humanity: gravity. Or watch Rocca ambush John McCain on the campaign trail and demand he name Iceland's best musical export (correct answer: Bjork). It was brilliant moment. Indeed, the show's masterful through the skewed filter of comedy than through Tom Brokaw's solemn pronouncements. And Stewart, like his namesake Swift, may be his era's best truth teller. [Or like his namesake Livingston Seagull, may be this era's best provider of painfully obvious pop-psycho platitudes.]

Despite Stewart's initial uncertainty about doing this article, I'm starting to think he's not a diva after all. Ask his friends; they'll tell you. Neurotic, sleep-deprived, insecure, worried he's getting old, afflicted with a touch of the sad-clown syndrome, yes. [You nailed it!! Have you been reading my courage journal?] But diva? Not this mench. "He asks about every tiny detail of things that are important in your life," says Madeline Smithberg, executive producer of The Daily Show, "and he isn't feigning. He knows the eating habits of everyone and he knows when all the camera guys are pooping." [Because someday that will be a question on Millionaire, and I will answer it and win.]

And he does ask about my life, He asks about my my wife, Julie, my apartment my heath, [When are you pooping?] my magazine. He wants to know whom we would have put on the cover if not him. I tell him we were considering not having a photo, just a typewritten text. "It was me or Helvetica?" he says. "I'm much easier to work with than Helvetica. Helvetica demands hair, makeup, the works." No doubt about it: Helvetica is the funniest font. [Times Roman is the most dignified font. Chicago the most enigmatic. Geneva gets laid the most.] Stewart just knows from funny: It's effortless for him. So how'd he develop that infallible humor sonar? Let's finally get to that childhood. [Noooooooo]

Jonathan Stewart Leibowitz was born in Trenton, new Jersey in 1963. [1962. Although I'm told I can play ... Enough with that joke.] His father was a physicist for RCA, his mother, an educational consultant. In high school, Stewart wasn't exactly homecoming king. We're talking a concave chest, skin with the topography of the Swiss Alps [ouch], the whole geeky shebang. Which, of course created the best recipe for a comedic mind, instilling in the young suburbanite a perfectly balanced mixture of self-loathing and the craving for love. [Blah, blah]

Stewart attended William & Mary, [Ouch] graduated, suffered through a daytime bartending gig at a Mexican restaurant, then moved to New York. Stewart himself did some heavy drinking during this period. He also ingested chemicals not sanctioned by the FDA a practice he insists he stopped. [Mostly mercury. Beat that, Downey Jr.] He tried stand-up for the first time at the Bitter End, bombed, went back, got better, earned a little extra scratch doing a kiddie show with disabled puppets, and finally scored again hosting his own successful MTV talk show. Which he promptly ditched. He left behind to take on the Big Boys -- Leno and Letterman -- with a syndicated talk show. Not smart. No one watched. Things got so bad, Stewart tried to scare up some ratings with a little stunt: One of his writers came out as the first guest . . . dressed as Hitler. Stewart asked Hitler about his upcoming project. "Czechoslovakia, Poland," said Hitler. "You never know with me." Stewart's bosses called before the taping was over-and they were not amused. The Hitler sketch never aired. [A sentence you'll find in almost every article in Esquire.] Soon after, Stewart learned about the cancellation of his show from the New York Post.

So he cast about for a while. He wrote a book titled Naked Pictures of Famous People which he calls a "shitty Without Feathers," but which is actually the best of all books by standup comics. The piece on Martha Stewart's Vagina is worth the price of admission. He appeared semiregularly on the ingenious Larry Sanders Show. He popped up in handful of movies of no major consequence. (The Faculty, anyone?) [Even I'm no longer paying attention -- and this is my life] He was completely edited out of the First Wives Club. [I also spent some time as a drug mule. When I quit they gave me a gold-plated condom. I still have it up my ass. Sentimental value.]

And then he took over on The Daily Show from six-foot-four blonde guy named Craig Kilborn, who left behind a gift: a phone book for Stewart to sit on.

Stewart is now sitting behind the Daily Show desk, no phone book necessary. When he first arrived, he had a smaller desk built, which he says is typical Stewartian fashion, looks like furniture from a dollhouse. [Let me guess. I'm really not a tall man!!] He's wearing a beige Canali suit, a rust colored tie, and black hiking boots. His hair is swooped back in a mini pompadour. [The year is 1953.]

It's right before a taping, and Stewart's doing a free form warm-up shtick that ranges in topic from Ebola to wacky ties. The audience is laughing. But for some reason, the right side of the crowd is laughing harder than the left side. Stewart picks up on this. "This side still can't believe they couldn't get tickets to Conan," he shouts. "They cannot be entertained! They are unentertainable. They are ringers from the third season of Make Me Laugh!" He walks over to the left side,"But I do want to welcome a big group from the Stoics convention."

To give them a jolt, Stewart resorts to slapstick. He tells the audience that he gets into his anchor chair the same way Starsky and Hutch got in their car. He runs toward the desk, jumps slide his ass across the desktop and lands in the chair-exactly wrong way, wit the groin against the chairs back. "Do you need both testicles?", he wheezes. [Note to self: Get high after show, not before. It's affection your warm-up.]

Crotch humor aside, what's The Daily Show's appeal to this fresh-out-the-dorm audience? Ask Stewart and you'll get this answer: "Because kids today love media analysis. I say, to them, 'Who's your favorite celebrity?' and without fail they say, 'Howie Kurtz.'" Howard Kurtz is the media critic for The Washington Post and perhaps the most boring man alive. [You've obviously never asked Mark Russell what's new.] Stewart continues: "Eminem and Howie Kurtz, but I gotta say, Howie Kurtz more thank Eminem. An the weird thing is, they're all imitating Howie. There was an eleven-year-old kid in Oklahoma who nearly killed himself criticizing the Post's reporting of the Bush DWI scandal."

The real answer is this: People are fed up with the news. As is Stewart. He hates its relentlessness, its pomposity, it's onanism, [Did you just slip a reference to jerking off? That is so awesome.] its faux concern, its co-option of show-business salesmanship [I do like their theme music.] -- and his anger fuels his humor, giving it depth, subversive power, and righteousness. "He has this internal barometer of what's right and what's wrong," says Smithberg. "He has a very sensitive justice meter. He's just way to smart for that little body." [Are you all suggesting I lack physical size?] But unlike, say, Dennis Miller, when Stewart lashes out, it's a tempered rage. "When he tells a joke that compromising to somebody its done with a certain level of shame," [Everything in my life is done with a certain level of shame ....] says Gillian Anderson, who starred opposite Stewart in 1998's mediocre Playing By Heart. "It's kind of got a built-in apology to it."

Stewart himself will soon be making the rounds on other talk shows, promoting Death to Smoochy, a Danny Devito-directed movie in which he plays a sleazy network executive. So far, his acting career hasn't exactly achieved liftoff [Clearly you never saw my turn as Rollerblader #1 in Mixed Nuts.] mostly because he's chosen a string of mediocre movies. He's not as bad actor, truth to tell, though he's best when playing some version of Jon Stewart. So what will the real Jon Stewart be doing in five years? Will he grow restless as the king of basic cable? "I'm looking to branch out into dramatic tearjerker roles," Stewart says. "Never having been able to pull something like that off, even in real life, I now would like to try it. Because why would you want to do the thing you're good at? Do the other thing, the thing you're not good at." Typical Stewart. A nonanswer, slightly off topic. But it's just clever enough that you gotta forgive the guy -- and hope that he never runs out of Skittles. [I promised myself I wasn't gonna cry, but ... that line is going in the courage journal.]


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Copyright © 2001 Esquire. All rights reserved.
Thanks to Chaney for the article.

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